Need ideas/suggestions for local sailing adventure regatta

[RussH]

Through my association with a local news/blog website, I have proposed a sailing adventure race. I have participated in many adventure races and triathlons but now that I'm a bit..uhmmm...older...I'm more inclined to organize and participate in endeavors of fun not pain.
The regatta would take place on the coastal and near coastal waters around Beaufort, South Carolina. The event would encompass 3 days and two nights. The PluffMud Adventure would require the participant to sail to daily destinations, establish camp, and complete a few tasks. Designed as a solo event and boats less than 18 feet, there will be waivers for everything after all this is for fun. As was the Golden Globe race there will be a window in which anyone can complete the course, say from 4th of July through Labor day. Each participant will document their achievement through pics or blog entries or both. The course will require the participant to "circumnavigate" St Helena, Lady's, and Bay Point Islands, via overnight stays at Otter Is and Bull Pt.
How do you present such a regatta to your news/bog site audience?
What obstacles/ events would you have the participants face?
What equipment would you make mandatory aside from legal safety equipment?
Remember everything should be fun, challenging but fun.
btw there will be no entry fee nor prize money. Just the awarding of the coveted "rotted tiller" which I have since I just bought a new on from Rudy.
Thanks and please help.